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Acta Crystallogr Sect E Struct Rep Online. 2012 February 1; 68(Pt 2): o308–o309.
Published online 2012 January 7. doi:  10.1107/S1600536811055966
PMCID: PMC3275001

Ethyl 2-(4-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate

Abstract

The asymmetric unit of the title compound, C24H27N3O4, contains two mol­ecules, A and B. The benzimidazole rings are essentially planar [maximum deviations = 0.0144 (10) and 0.0311 (8) Å in A and B, respectively]. The dihedral angle between the benzimidazole mean plane and its attached benzene ring is 36.90 (5) ° for mol­ecule A and 51.40 (5) ° for mol­ecule B. In both mol­ecules, the pyrrolidine ring adopts an envelope conformation with a C atom as the flap. In molecule B, the flap C atom is disordered over two positions in a 0.711 (6):0.289 (6) ratio. In the crystal, C—H(...)O inter­actions link the mol­ecules, generating [100] chains. The crystal packing also features weak π–π inter­actions between the imidazole and benzene rings [centroid–centroid distances = 3.8007 (7) and 3.8086 (7) Å] and between the benzene rings [centroid–centroid distance = 3.7001 (7) Å] and C—H(...)π inter­actions involving the benzene rings.

Related literature

For the biological activity of benzimidazole derivatives, see: Spasov et al. (1999 [triangle]); Tanious et al. (2004) [triangle]; Townsend & Revankar (1970 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-0o308-scheme1.jpg

Experimental

Crystal data

  • C24H27N3O4
  • M r = 421.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-0o308-efi1.jpg
  • a = 10.7455 (3) Å
  • b = 12.2235 (3) Å
  • c = 16.1967 (4) Å
  • α = 86.162 (1)°
  • β = 80.917 (1)°
  • γ = 88.275 (1)°
  • V = 2095.60 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.74 × 0.43 × 0.14 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.935, T max = 0.987
  • 47137 measured reflections
  • 11119 independent reflections
  • 9491 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.133
  • S = 1.02
  • 11119 reflections
  • 573 parameters
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055966/hb6575sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055966/hb6575Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055966/hb6575Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grants Nos.1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti of Sains Malaysia, Penang.

supplementary crystallographic information

Comment

The benzimidazole nucleus is an important pharmacophore in drug discovery (Spasov et al., 1999). Substituted benzimidazole is the key building block for numerous compounds which plays crucial roles in the function of biologically important molecules (Tanious et al., 2004). In particular, substituted benzimidazoles are recognized as potential anticancer agents (Townsend & Revankar, 1970). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented here.

The asymmetric unit of the title compound consist two crystallographically independent molecules (A and B). The benzimidazoles N1A–N2A/C1A–C7A and N1B–N2B/C1B–C7B rings are essentially planar with maximum deviations of 0.0144 (10) and 0.0311 (8) Å at atoms N1A and C3B, respectively. In molecule A, the dihedral angle between the mean plane through the benzimidazole, (N1A–N2A/C1A–C7A) ring with the mean plane through the benzene, (C8A–C13A) ring is 36.90 (5) °. In molecule B, the dihedral angle between the corresponding rings is 51.40 (5) °. Atom C21B is disordered (Fig. 2) over two positions, with occupancy ratios of 0.711 (6):0.289 (6). The pyrrolidin moiety in both molecules adopts an envelope conformation. In molecule A, the puckering parameters Q = 0.3051 (14) Å and [var phi] = 245.2 (2)° with C21A at the flap. In molecule B, the puckering parameters for the disordered pyrrolidin ring are Q = 0.2696 (16) Å and [var phi] = 247.9 (3)° with C21B at the flap and Q = 0.248 (3) Å and [var phi] = 78.7 (4)° with C21X at the flap (Cremer & Pople, 1975).

In the crystal packing (Fig. 2), R22(10) ring motifs (Bernstein et al., 1995) are formed by C19A—H19B···O3B (x-1,y,z) and C19B—H19C···O3A(1+x,y,z) intermolecular interactions. C5A—H5AA···O3B(x-1,y,z), C5B—H5BA···O3A(1+x,y,z) and C19A—H19A···O2A (x-1,y,z) interactions further link the molecules into ribbon along the a axis. π–π interactions are observed within the benzimidazole rings system between the imidazole, (N1B–N2B/C1B/C6B–C7B; centroid Cg1 and N1A–N2A/C1A/C6A–C7A; centroid Cg3) and the benzene, (C1A–C6A;centroid Cg2 and C1B–C6B;centroid Cg4) rings with Cg1···Cg2 distance of 3.8007 (7) Å and Cg3···Cg4 distance of 3.8085 (7) Å. π–π interactions are also observed between the benzene rings with a Cg4···Cg2 distance of 3.7001 (7) Å. The crystal packing are further stabilized by weak C—H···π interactions (Table 1) involving benzimidazole and benzene rings.

Experimental

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-methoxybenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 hrs. After completion, the reaction mixture was diluted in Ethyl acetate (20 mL) and washed with water (20 mL). The organic layer was collected, dried over Na2SO4 and the evaporated in vacuo to yield the product. The product was recrystallised from ethyl acetate to form yellow plates.

Refinement

Atom C21B is disodered over two positions, with occupancy ratios of 0.711 (6):0.289 (6). All the H atoms positioned geometrically and refined using a riding model with with C–H = 0.95–0.99 Å. The Uiso values were constrained to be 1.5Ueq (methyl-H atom) and 1.2Ueq (other H atoms). The rotating model group was applied for the methyl groups.

Figures

Fig. 1.
The structure of the title compound, showing 50% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.
Fig. 2.
The crystal packing, viewed along the b-axis, showing the molecules are connected into ribbon along a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C24H27N3O4Z = 4
Mr = 421.49F(000) = 896
Triclinic, P1Dx = 1.336 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7455 (3) ÅCell parameters from 9863 reflections
b = 12.2235 (3) Åθ = 2.5–32.8°
c = 16.1967 (4) ŵ = 0.09 mm1
α = 86.162 (1)°T = 100 K
β = 80.917 (1)°Plate, yellow
γ = 88.275 (1)°0.74 × 0.43 × 0.14 mm
V = 2095.60 (9) Å3

Data collection

Bruker SMART APEXII CCD diffractometer11119 independent reflections
Radiation source: fine-focus sealed tube9491 reflections with I > 2σ(I)
graphiteRint = 0.026
[var phi] and ω scansθmax = 29.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −14→14
Tmin = 0.935, Tmax = 0.987k = −16→16
47137 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0777P)2 + 0.709P] where P = (Fo2 + 2Fc2)/3
11119 reflections(Δ/σ)max < 0.001
573 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = −0.27 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O1A0.43138 (8)0.57270 (7)0.36306 (6)0.0251 (2)
O2A0.55442 (8)0.43980 (7)0.41340 (6)0.02447 (19)
O3A−0.31842 (9)0.15173 (7)0.21854 (6)0.02455 (19)
O4A0.02719 (8)−0.37276 (7)0.40345 (6)0.02395 (19)
N1A0.27573 (9)0.09583 (8)0.39577 (6)0.01564 (19)
N2A0.09660 (8)0.16243 (7)0.35276 (6)0.01339 (18)
N3A−0.30856 (9)0.11955 (8)0.35853 (6)0.01669 (19)
C1A0.28242 (10)0.20905 (9)0.38208 (7)0.0144 (2)
C2A0.37755 (10)0.28003 (9)0.39205 (7)0.0164 (2)
H2AA0.45250.25300.41120.020*
C3A0.35928 (10)0.39193 (9)0.37303 (7)0.0157 (2)
C4A0.24819 (10)0.43191 (9)0.34413 (7)0.0159 (2)
H4AA0.23900.50830.33080.019*
C5A0.15220 (10)0.36284 (9)0.33465 (7)0.0149 (2)
H5AA0.07730.38990.31550.018*
C6A0.17139 (10)0.25157 (9)0.35475 (7)0.0134 (2)
C7A0.16384 (10)0.07135 (9)0.37803 (7)0.0144 (2)
C8A0.11945 (10)−0.04209 (9)0.38429 (7)0.0150 (2)
C9A−0.00483 (10)−0.07252 (9)0.41281 (7)0.0165 (2)
H9AA−0.0670−0.01720.42730.020*
C10A−0.04016 (11)−0.18211 (9)0.42064 (7)0.0169 (2)
H10A−0.1252−0.20090.44050.020*
C11A0.05013 (11)−0.26363 (9)0.39907 (7)0.0174 (2)
C12A0.17569 (11)−0.23495 (10)0.37145 (8)0.0207 (2)
H12A0.2378−0.29050.35750.025*
C13A0.20951 (11)−0.12620 (9)0.36439 (8)0.0186 (2)
H13A0.2951−0.10780.34580.022*
C14A0.45920 (11)0.46763 (9)0.38589 (8)0.0184 (2)
C15A0.52194 (12)0.65402 (10)0.37453 (9)0.0266 (3)
H15A0.55950.63270.42540.032*
H15B0.47850.72600.38250.032*
C16A0.62410 (13)0.66355 (11)0.29988 (9)0.0290 (3)
H16A0.68020.72300.30640.043*
H16B0.58630.67940.24900.043*
H16C0.67250.59440.29540.043*
C17A−0.02866 (10)0.17174 (9)0.32769 (7)0.0142 (2)
H17A−0.05350.09910.31290.017*
H17B−0.02570.22280.27740.017*
C18A−0.12686 (10)0.21337 (9)0.39798 (7)0.0153 (2)
H18A−0.12990.16190.44810.018*
H18B−0.10120.28560.41300.018*
C19A−0.25791 (10)0.22453 (9)0.37307 (8)0.0168 (2)
H19A−0.31580.25930.41800.020*
H19B−0.25390.27330.32140.020*
C20A−0.35991 (13)0.04285 (10)0.42742 (8)0.0249 (3)
H20A−0.43950.07170.45860.030*
H20B−0.29890.02680.46670.030*
C21A−0.38274 (14)−0.05892 (10)0.38240 (8)0.0273 (3)
H21A−0.3070−0.10760.37550.033*
H21B−0.4549−0.10070.41340.033*
C22A−0.41136 (12)−0.01174 (10)0.29818 (8)0.0224 (2)
H22A−0.50300.00150.29980.027*
H22B−0.3806−0.06170.25340.027*
C23A−0.34068 (10)0.09538 (9)0.28431 (8)0.0170 (2)
C24A−0.09938 (12)−0.40763 (10)0.43130 (8)0.0243 (3)
H24A−0.1026−0.48750.43000.037*
H24B−0.1550−0.37290.39430.037*
H24C−0.1271−0.38630.48870.037*
O1B0.11742 (8)0.00048 (7)0.14833 (6)0.02285 (19)
O2B0.00913 (9)0.12746 (7)0.07933 (6)0.0249 (2)
O3B0.89232 (9)0.42845 (7)0.26430 (6)0.02442 (19)
O4B0.52357 (8)0.94651 (7)0.10398 (6)0.02073 (18)
N1B0.26036 (9)0.47944 (7)0.11609 (6)0.01480 (18)
N2B0.44823 (8)0.41675 (7)0.14796 (6)0.01313 (18)
N3B0.85576 (9)0.46961 (8)0.12995 (6)0.01700 (19)
C1B0.25893 (10)0.36593 (9)0.12809 (7)0.0135 (2)
C2B0.16548 (10)0.29273 (9)0.11952 (7)0.0143 (2)
H2BA0.08730.31810.10420.017*
C3B0.19026 (10)0.18126 (9)0.13407 (7)0.0144 (2)
C4B0.30537 (10)0.14328 (9)0.15872 (7)0.0150 (2)
H4BA0.31790.06700.17070.018*
C5B0.40013 (10)0.21455 (9)0.16585 (7)0.0148 (2)
H5BA0.47800.18910.18150.018*
C6B0.37524 (10)0.32567 (9)0.14884 (7)0.0130 (2)
C7B0.37424 (10)0.50635 (9)0.12798 (7)0.0137 (2)
C8B0.41785 (10)0.61994 (9)0.12023 (7)0.0141 (2)
C9B0.53045 (10)0.65103 (9)0.07059 (7)0.0154 (2)
H9BA0.58200.59690.04160.018*
C10B0.56981 (10)0.75954 (9)0.06227 (7)0.0156 (2)
H10B0.64690.77910.02790.019*
C11B0.49422 (11)0.83879 (9)0.10526 (7)0.0161 (2)
C12B0.37896 (11)0.80928 (9)0.15378 (8)0.0208 (2)
H12B0.32660.86360.18200.025*
C13B0.34122 (11)0.70155 (9)0.16080 (8)0.0192 (2)
H13B0.26260.68250.19340.023*
C14B0.09513 (11)0.10324 (9)0.11753 (7)0.0166 (2)
C15B0.03339 (12)−0.08339 (10)0.13095 (9)0.0244 (3)
H15C0.0753−0.15630.13520.029*
H15D0.0149−0.07000.07310.029*
C16B−0.08748 (13)−0.08261 (11)0.19151 (9)0.0287 (3)
H16D−0.1410−0.14160.18020.043*
H16E−0.1314−0.01190.18500.043*
H16F−0.0690−0.09380.24890.043*
C17B0.57713 (10)0.41302 (9)0.16718 (7)0.0143 (2)
H17C0.58060.36420.21810.017*
H17D0.60050.48740.17910.017*
C18B0.67204 (10)0.37172 (9)0.09507 (7)0.0149 (2)
H18C0.67030.42190.04470.018*
H18D0.64690.29840.08190.018*
C19B0.80624 (10)0.36410 (9)0.11548 (7)0.0162 (2)
H19C0.80750.31420.16610.019*
H19D0.86230.33160.06850.019*
C20B0.86896 (11)0.56181 (10)0.06720 (8)0.0199 (2)
H20C0.78800.60240.06630.024*0.711 (6)
H20D0.90050.53720.01060.024*0.711 (6)
H20E0.79290.57230.04330.024*0.289 (6)
H20F0.93700.54720.02300.024*0.289 (6)
C21B0.9682 (2)0.63305 (15)0.09897 (11)0.0199 (5)0.711 (6)
H21C1.05470.61430.07200.024*0.711 (6)
H21D0.95140.71220.08700.024*0.711 (6)
C21X0.8945 (5)0.6602 (4)0.1078 (3)0.0220 (13)0.289 (6)
H21E0.81650.70370.12450.026*0.289 (6)
H21F0.95690.70700.07110.026*0.289 (6)
C22B0.95215 (12)0.60541 (10)0.19016 (8)0.0227 (2)
H22C0.89370.65840.22080.027*0.711 (6)
H22D1.03410.60580.21070.027*0.711 (6)
H22E1.04260.60220.17960.027*0.289 (6)
H22F0.92500.64620.23860.027*0.289 (6)
C23B0.89772 (10)0.49098 (9)0.20152 (8)0.0176 (2)
C24B0.64097 (12)0.98164 (10)0.05625 (8)0.0232 (2)
H24D0.65311.05900.06480.035*
H24E0.63990.9728−0.00330.035*
H24F0.71010.93720.07460.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0202 (4)0.0133 (4)0.0431 (6)−0.0036 (3)−0.0094 (4)−0.0003 (4)
O2A0.0184 (4)0.0217 (4)0.0351 (5)0.0006 (3)−0.0088 (4)−0.0047 (4)
O3A0.0289 (5)0.0235 (4)0.0225 (5)−0.0046 (3)−0.0100 (4)0.0054 (3)
O4A0.0241 (4)0.0126 (4)0.0340 (5)−0.0021 (3)−0.0001 (4)−0.0035 (3)
N1A0.0153 (4)0.0134 (4)0.0182 (5)0.0009 (3)−0.0029 (3)−0.0001 (3)
N2A0.0130 (4)0.0119 (4)0.0152 (4)0.0000 (3)−0.0021 (3)−0.0003 (3)
N3A0.0168 (4)0.0146 (4)0.0183 (5)−0.0031 (3)−0.0025 (4)0.0019 (3)
C1A0.0140 (5)0.0131 (5)0.0156 (5)0.0013 (4)−0.0014 (4)−0.0006 (4)
C2A0.0129 (5)0.0168 (5)0.0196 (5)0.0011 (4)−0.0033 (4)−0.0011 (4)
C3A0.0141 (5)0.0146 (5)0.0183 (5)−0.0007 (4)−0.0014 (4)−0.0020 (4)
C4A0.0162 (5)0.0137 (5)0.0174 (5)0.0003 (4)−0.0016 (4)−0.0003 (4)
C5A0.0153 (5)0.0136 (5)0.0159 (5)0.0010 (4)−0.0028 (4)0.0000 (4)
C6A0.0131 (5)0.0137 (5)0.0129 (5)−0.0007 (4)−0.0007 (4)−0.0009 (4)
C7A0.0157 (5)0.0133 (5)0.0135 (5)0.0012 (4)−0.0008 (4)−0.0005 (4)
C8A0.0170 (5)0.0135 (5)0.0141 (5)0.0012 (4)−0.0024 (4)0.0002 (4)
C9A0.0170 (5)0.0142 (5)0.0173 (5)0.0023 (4)−0.0008 (4)0.0001 (4)
C10A0.0168 (5)0.0170 (5)0.0163 (5)−0.0001 (4)−0.0014 (4)0.0005 (4)
C11A0.0211 (5)0.0135 (5)0.0174 (5)−0.0009 (4)−0.0025 (4)−0.0009 (4)
C12A0.0199 (5)0.0146 (5)0.0266 (6)0.0023 (4)0.0002 (4)−0.0046 (4)
C13A0.0171 (5)0.0157 (5)0.0221 (6)0.0010 (4)0.0002 (4)−0.0023 (4)
C14A0.0171 (5)0.0159 (5)0.0218 (6)−0.0006 (4)−0.0005 (4)−0.0039 (4)
C15A0.0232 (6)0.0175 (6)0.0407 (8)−0.0054 (4)−0.0075 (5)−0.0057 (5)
C16A0.0299 (7)0.0263 (7)0.0319 (7)−0.0080 (5)−0.0067 (5)−0.0025 (5)
C17A0.0134 (5)0.0145 (5)0.0152 (5)0.0002 (4)−0.0034 (4)−0.0006 (4)
C18A0.0151 (5)0.0136 (5)0.0174 (5)0.0006 (4)−0.0032 (4)−0.0016 (4)
C19A0.0145 (5)0.0133 (5)0.0228 (6)0.0002 (4)−0.0040 (4)−0.0003 (4)
C20A0.0349 (7)0.0192 (6)0.0188 (6)−0.0076 (5)0.0016 (5)0.0020 (4)
C21A0.0393 (7)0.0172 (6)0.0239 (6)−0.0076 (5)0.0004 (5)0.0007 (5)
C22A0.0207 (6)0.0207 (6)0.0264 (6)−0.0060 (4)−0.0046 (5)−0.0006 (5)
C23A0.0127 (5)0.0170 (5)0.0218 (6)0.0000 (4)−0.0047 (4)0.0009 (4)
C24A0.0275 (6)0.0192 (6)0.0255 (6)−0.0067 (5)−0.0003 (5)−0.0015 (5)
O1B0.0219 (4)0.0138 (4)0.0349 (5)−0.0040 (3)−0.0111 (4)0.0006 (3)
O2B0.0248 (4)0.0216 (4)0.0311 (5)−0.0033 (3)−0.0136 (4)0.0008 (4)
O3B0.0269 (5)0.0238 (4)0.0242 (5)−0.0018 (3)−0.0112 (4)0.0039 (3)
O4B0.0247 (4)0.0118 (4)0.0246 (4)−0.0027 (3)0.0000 (3)−0.0020 (3)
N1B0.0148 (4)0.0128 (4)0.0164 (5)0.0003 (3)−0.0018 (3)0.0003 (3)
N2B0.0123 (4)0.0112 (4)0.0157 (4)0.0003 (3)−0.0022 (3)0.0001 (3)
N3B0.0186 (4)0.0141 (4)0.0185 (5)−0.0044 (3)−0.0039 (4)0.0021 (3)
C1B0.0132 (5)0.0135 (5)0.0132 (5)0.0010 (4)−0.0011 (4)0.0002 (4)
C2B0.0129 (5)0.0147 (5)0.0148 (5)0.0006 (4)−0.0015 (4)0.0000 (4)
C3B0.0143 (5)0.0147 (5)0.0140 (5)−0.0009 (4)−0.0012 (4)−0.0008 (4)
C4B0.0163 (5)0.0129 (5)0.0155 (5)0.0004 (4)−0.0023 (4)−0.0004 (4)
C5B0.0142 (5)0.0139 (5)0.0159 (5)0.0015 (4)−0.0023 (4)0.0003 (4)
C6B0.0128 (5)0.0137 (5)0.0123 (5)−0.0003 (4)−0.0013 (4)−0.0005 (4)
C7B0.0142 (5)0.0129 (5)0.0134 (5)0.0017 (4)−0.0013 (4)0.0000 (4)
C8B0.0150 (5)0.0123 (5)0.0152 (5)0.0008 (4)−0.0033 (4)0.0004 (4)
C9B0.0171 (5)0.0132 (5)0.0152 (5)0.0014 (4)−0.0011 (4)−0.0011 (4)
C10B0.0164 (5)0.0146 (5)0.0153 (5)−0.0007 (4)−0.0019 (4)0.0008 (4)
C11B0.0195 (5)0.0116 (5)0.0177 (5)−0.0003 (4)−0.0045 (4)−0.0004 (4)
C12B0.0214 (5)0.0141 (5)0.0252 (6)0.0026 (4)0.0020 (5)−0.0033 (4)
C13B0.0166 (5)0.0161 (5)0.0232 (6)0.0010 (4)0.0018 (4)−0.0012 (4)
C14B0.0173 (5)0.0151 (5)0.0172 (5)−0.0007 (4)−0.0017 (4)−0.0015 (4)
C15B0.0236 (6)0.0158 (5)0.0356 (7)−0.0048 (4)−0.0091 (5)−0.0035 (5)
C16B0.0305 (7)0.0244 (6)0.0314 (7)−0.0083 (5)−0.0037 (5)−0.0019 (5)
C17B0.0127 (5)0.0157 (5)0.0150 (5)−0.0002 (4)−0.0041 (4)−0.0002 (4)
C18B0.0141 (5)0.0145 (5)0.0162 (5)0.0002 (4)−0.0031 (4)−0.0010 (4)
C19B0.0136 (5)0.0132 (5)0.0220 (6)−0.0010 (4)−0.0039 (4)−0.0006 (4)
C20B0.0208 (5)0.0178 (5)0.0202 (6)−0.0027 (4)−0.0027 (4)0.0041 (4)
C21B0.0223 (12)0.0154 (8)0.0217 (9)−0.0054 (7)−0.0025 (7)0.0004 (6)
C21X0.023 (3)0.017 (2)0.026 (2)−0.0044 (18)−0.0045 (18)0.0040 (16)
C22B0.0206 (6)0.0190 (6)0.0299 (7)−0.0036 (4)−0.0075 (5)−0.0023 (5)
C23B0.0121 (5)0.0180 (5)0.0232 (6)−0.0003 (4)−0.0040 (4)−0.0012 (4)
C24B0.0262 (6)0.0182 (6)0.0246 (6)−0.0068 (4)−0.0013 (5)−0.0012 (4)

Geometric parameters (Å, °)

O1A—C14A1.3506 (14)O4B—C11B1.3611 (13)
O1A—C15A1.4524 (14)O4B—C24B1.4331 (15)
O2A—C14A1.2099 (14)N1B—C7B1.3229 (14)
O3A—C23A1.2238 (15)N1B—C1B1.3883 (13)
O4A—C11A1.3590 (13)N2B—C6B1.3790 (13)
O4A—C24A1.4318 (15)N2B—C7B1.3847 (13)
N1A—C7A1.3266 (14)N2B—C17B1.4656 (13)
N1A—C1A1.3890 (14)N3B—C23B1.3519 (15)
N2A—C6A1.3783 (13)N3B—C19B1.4568 (14)
N2A—C7A1.3832 (13)N3B—C20B1.4608 (15)
N2A—C17A1.4651 (13)C1B—C2B1.3939 (15)
N3A—C23A1.3550 (15)C1B—C6B1.4109 (14)
N3A—C19A1.4565 (14)C2B—C3B1.3920 (15)
N3A—C20A1.4579 (15)C2B—H2BA0.9500
C1A—C2A1.3957 (15)C3B—C4B1.4147 (15)
C1A—C6A1.4101 (14)C3B—C14B1.4851 (15)
C2A—C3A1.3968 (15)C4B—C5B1.3832 (15)
C2A—H2AA0.9500C4B—H4BA0.9500
C3A—C4A1.4120 (15)C5B—C6B1.3941 (14)
C3A—C14A1.4861 (15)C5B—H5BA0.9500
C4A—C5A1.3857 (15)C7B—C8B1.4698 (15)
C4A—H4AA0.9500C8B—C9B1.3908 (15)
C5A—C6A1.3941 (14)C8B—C13B1.4044 (15)
C5A—H5AA0.9500C9B—C10B1.3958 (15)
C7A—C8A1.4718 (15)C9B—H9BA0.9500
C8A—C9A1.3954 (15)C10B—C11B1.3955 (15)
C8A—C13A1.4083 (15)C10B—H10B0.9500
C9A—C10A1.3955 (15)C11B—C12B1.4012 (16)
C9A—H9AA0.9500C12B—C13B1.3817 (16)
C10A—C11A1.3920 (15)C12B—H12B0.9500
C10A—H10A0.9500C13B—H13B0.9500
C11A—C12A1.4001 (16)C15B—C16B1.4991 (19)
C12A—C13A1.3813 (16)C15B—H15C0.9900
C12A—H12A0.9500C15B—H15D0.9900
C13A—H13A0.9500C16B—H16D0.9800
C15A—C16A1.500 (2)C16B—H16E0.9800
C15A—H15A0.9900C16B—H16F0.9800
C15A—H15B0.9900C17B—C18B1.5269 (15)
C16A—H16A0.9800C17B—H17C0.9900
C16A—H16B0.9800C17B—H17D0.9900
C16A—H16C0.9800C18B—C19B1.5283 (14)
C17A—C18A1.5279 (15)C18B—H18C0.9900
C17A—H17A0.9900C18B—H18D0.9900
C17A—H17B0.9900C19B—H19C0.9900
C18A—C19A1.5248 (15)C19B—H19D0.9900
C18A—H18A0.9900C20B—C21X1.462 (4)
C18A—H18B0.9900C20B—C21B1.565 (2)
C19A—H19A0.9900C20B—H20C0.9900
C19A—H19B0.9900C20B—H20D0.9900
C20A—C21A1.5282 (18)C20B—H20E0.9600
C20A—H20A0.9900C20B—H20F0.9600
C20A—H20B0.9900C21B—C22B1.477 (2)
C21A—C22A1.5181 (19)C21B—H21C0.9900
C21A—H21A0.9900C21B—H21D0.9900
C21A—H21B0.9900C21X—C22B1.652 (5)
C22A—C23A1.5193 (16)C21X—H21E0.9900
C22A—H22A0.9900C21X—H21F0.9900
C22A—H22B0.9900C22B—C23B1.5209 (16)
C24A—H24A0.9800C22B—H22C0.9900
C24A—H24B0.9800C22B—H22D0.9900
C24A—H24C0.9800C22B—H22E0.9601
O1B—C14B1.3490 (14)C22B—H22F0.9599
O1B—C15B1.4560 (14)C24B—H24D0.9800
O2B—C14B1.2099 (14)C24B—H24E0.9800
O3B—C23B1.2255 (15)C24B—H24F0.9800
C14A—O1A—C15A116.38 (10)C2B—C3B—C4B121.21 (10)
C11A—O4A—C24A118.17 (9)C2B—C3B—C14B117.62 (10)
C7A—N1A—C1A104.81 (9)C4B—C3B—C14B121.05 (10)
C6A—N2A—C7A106.44 (9)C5B—C4B—C3B121.62 (10)
C6A—N2A—C17A123.00 (9)C5B—C4B—H4BA119.2
C7A—N2A—C17A130.56 (9)C3B—C4B—H4BA119.2
C23A—N3A—C19A123.60 (10)C4B—C5B—C6B116.45 (10)
C23A—N3A—C20A112.69 (10)C4B—C5B—H5BA121.8
C19A—N3A—C20A121.86 (10)C6B—C5B—H5BA121.8
N1A—C1A—C2A130.19 (10)N2B—C6B—C5B131.51 (10)
N1A—C1A—C6A110.04 (9)N2B—C6B—C1B105.57 (9)
C2A—C1A—C6A119.77 (10)C5B—C6B—C1B122.92 (10)
C1A—C2A—C3A118.01 (10)N1B—C7B—N2B113.22 (9)
C1A—C2A—H2AA121.0N1B—C7B—C8B123.28 (9)
C3A—C2A—H2AA121.0N2B—C7B—C8B123.51 (9)
C2A—C3A—C4A120.96 (10)C9B—C8B—C13B118.28 (10)
C2A—C3A—C14A117.88 (10)C9B—C8B—C7B122.23 (9)
C4A—C3A—C14A121.14 (10)C13B—C8B—C7B119.42 (10)
C5A—C4A—C3A121.85 (10)C8B—C9B—C10B121.81 (10)
C5A—C4A—H4AA119.1C8B—C9B—H9BA119.1
C3A—C4A—H4AA119.1C10B—C9B—H9BA119.1
C4A—C5A—C6A116.44 (10)C11B—C10B—C9B119.00 (10)
C4A—C5A—H5AA121.8C11B—C10B—H10B120.5
C6A—C5A—H5AA121.8C9B—C10B—H10B120.5
N2A—C6A—C5A131.32 (10)O4B—C11B—C10B124.63 (10)
N2A—C6A—C1A105.72 (9)O4B—C11B—C12B115.51 (10)
C5A—C6A—C1A122.95 (10)C10B—C11B—C12B119.86 (10)
N1A—C7A—N2A112.99 (10)C13B—C12B—C11B120.26 (10)
N1A—C7A—C8A122.22 (10)C13B—C12B—H12B119.9
N2A—C7A—C8A124.79 (10)C11B—C12B—H12B119.9
C9A—C8A—C13A117.70 (10)C12B—C13B—C8B120.74 (11)
C9A—C8A—C7A124.36 (10)C12B—C13B—H13B119.6
C13A—C8A—C7A117.85 (10)C8B—C13B—H13B119.6
C10A—C9A—C8A121.69 (10)O2B—C14B—O1B123.42 (10)
C10A—C9A—H9AA119.2O2B—C14B—C3B124.53 (11)
C8A—C9A—H9AA119.2O1B—C14B—C3B112.02 (9)
C11A—C10A—C9A119.53 (10)O1B—C15B—C16B110.85 (11)
C11A—C10A—H10A120.2O1B—C15B—H15C109.5
C9A—C10A—H10A120.2C16B—C15B—H15C109.5
O4A—C11A—C10A124.98 (10)O1B—C15B—H15D109.5
O4A—C11A—C12A115.35 (10)C16B—C15B—H15D109.5
C10A—C11A—C12A119.66 (10)H15C—C15B—H15D108.1
C13A—C12A—C11A120.20 (10)C15B—C16B—H16D109.5
C13A—C12A—H12A119.9C15B—C16B—H16E109.5
C11A—C12A—H12A119.9H16D—C16B—H16E109.5
C12A—C13A—C8A121.19 (11)C15B—C16B—H16F109.5
C12A—C13A—H13A119.4H16D—C16B—H16F109.5
C8A—C13A—H13A119.4H16E—C16B—H16F109.5
O2A—C14A—O1A123.37 (11)N2B—C17B—C18B111.97 (9)
O2A—C14A—C3A124.80 (11)N2B—C17B—H17C109.2
O1A—C14A—C3A111.83 (10)C18B—C17B—H17C109.2
O1A—C15A—C16A110.50 (11)N2B—C17B—H17D109.2
O1A—C15A—H15A109.5C18B—C17B—H17D109.2
C16A—C15A—H15A109.5H17C—C17B—H17D107.9
O1A—C15A—H15B109.5C17B—C18B—C19B112.42 (9)
C16A—C15A—H15B109.5C17B—C18B—H18C109.1
H15A—C15A—H15B108.1C19B—C18B—H18C109.1
C15A—C16A—H16A109.5C17B—C18B—H18D109.1
C15A—C16A—H16B109.5C19B—C18B—H18D109.1
H16A—C16A—H16B109.5H18C—C18B—H18D107.9
C15A—C16A—H16C109.5N3B—C19B—C18B113.49 (9)
H16A—C16A—H16C109.5N3B—C19B—H19C108.9
H16B—C16A—H16C109.5C18B—C19B—H19C108.9
N2A—C17A—C18A111.28 (9)N3B—C19B—H19D108.9
N2A—C17A—H17A109.4C18B—C19B—H19D108.9
C18A—C17A—H17A109.4H19C—C19B—H19D107.7
N2A—C17A—H17B109.4N3B—C20B—C21X108.55 (19)
C18A—C17A—H17B109.4N3B—C20B—C21B101.86 (10)
H17A—C17A—H17B108.0N3B—C20B—H20C111.4
C19A—C18A—C17A112.21 (9)C21X—C20B—H20C80.0
C19A—C18A—H18A109.2C21B—C20B—H20C111.4
C17A—C18A—H18A109.2N3B—C20B—H20D111.4
C19A—C18A—H18B109.2C21X—C20B—H20D131.3
C17A—C18A—H18B109.2C21B—C20B—H20D111.4
H18A—C18A—H18B107.9H20C—C20B—H20D109.3
N3A—C19A—C18A112.73 (9)N3B—C20B—H20E110.0
N3A—C19A—H19A109.0C21X—C20B—H20E110.0
C18A—C19A—H19A109.0C21B—C20B—H20E138.5
N3A—C19A—H19B109.0H20D—C20B—H20E81.2
C18A—C19A—H19B109.0N3B—C20B—H20F110.0
H19A—C19A—H19B107.8C21X—C20B—H20F110.0
N3A—C20A—C21A102.67 (10)C21B—C20B—H20F83.9
N3A—C20A—H20A111.2H20C—C20B—H20F131.2
C21A—C20A—H20A111.2H20E—C20B—H20F108.4
N3A—C20A—H20B111.2C22B—C21B—C20B104.43 (12)
C21A—C20A—H20B111.2C22B—C21B—H21C110.9
H20A—C20A—H20B109.1C20B—C21B—H21C110.9
C22A—C21A—C20A103.30 (10)C22B—C21B—H21D110.9
C22A—C21A—H21A111.1C20B—C21B—H21D110.9
C20A—C21A—H21A111.1H21C—C21B—H21D108.9
C22A—C21A—H21B111.1C20B—C21X—C22B101.0 (3)
C20A—C21A—H21B111.1C20B—C21X—H21E111.6
H21A—C21A—H21B109.1C22B—C21X—H21E111.6
C21A—C22A—C23A103.75 (10)C20B—C21X—H21F111.6
C21A—C22A—H22A111.0C22B—C21X—H21F111.6
C23A—C22A—H22A111.0H21E—C21X—H21F109.4
C21A—C22A—H22B111.0C21B—C22B—C23B104.81 (11)
C23A—C22A—H22B111.0C23B—C22B—C21X103.05 (17)
H22A—C22A—H22B109.0C21B—C22B—H22C110.8
O3A—C23A—N3A125.52 (11)C23B—C22B—H22C110.8
O3A—C23A—C22A126.59 (11)C21X—C22B—H22C83.6
N3A—C23A—C22A107.88 (10)C21B—C22B—H22D110.8
O4A—C24A—H24A109.5C23B—C22B—H22D110.8
O4A—C24A—H24B109.5C21X—C22B—H22D135.8
H24A—C24A—H24B109.5H22C—C22B—H22D108.9
O4A—C24A—H24C109.5C21B—C22B—H22E82.5
H24A—C24A—H24C109.5C23B—C22B—H22E111.1
H24B—C24A—H24C109.5C21X—C22B—H22E111.1
C14B—O1B—C15B116.14 (9)H22C—C22B—H22E130.4
C11B—O4B—C24B118.21 (9)C21B—C22B—H22F133.9
C7B—N1B—C1B104.69 (9)C23B—C22B—H22F111.2
C6B—N2B—C7B106.31 (9)C21X—C22B—H22F111.2
C6B—N2B—C17B124.17 (9)H22D—C22B—H22F82.4
C7B—N2B—C17B129.50 (9)H22E—C22B—H22F109.1
C23B—N3B—C19B123.55 (10)O3B—C23B—N3B125.50 (11)
C23B—N3B—C20B113.26 (9)O3B—C23B—C22B126.40 (11)
C19B—N3B—C20B123.16 (10)N3B—C23B—C22B108.10 (10)
N1B—C1B—C2B129.97 (10)O4B—C24B—H24D109.5
N1B—C1B—C6B110.21 (9)O4B—C24B—H24E109.5
C2B—C1B—C6B119.77 (10)H24D—C24B—H24E109.5
C3B—C2B—C1B117.91 (10)O4B—C24B—H24F109.5
C3B—C2B—H2BA121.0H24D—C24B—H24F109.5
C1B—C2B—H2BA121.0H24E—C24B—H24F109.5
C7A—N1A—C1A—C2A178.81 (12)C1B—C2B—C3B—C14B−174.69 (10)
C7A—N1A—C1A—C6A−0.57 (12)C2B—C3B—C4B—C5B−2.86 (17)
N1A—C1A—C2A—C3A179.72 (11)C14B—C3B—C4B—C5B173.15 (10)
C6A—C1A—C2A—C3A−0.95 (16)C3B—C4B—C5B—C6B1.04 (16)
C1A—C2A—C3A—C4A−0.36 (17)C7B—N2B—C6B—C5B−179.16 (11)
C1A—C2A—C3A—C14A178.38 (10)C17B—N2B—C6B—C5B−0.53 (18)
C2A—C3A—C4A—C5A1.03 (17)C7B—N2B—C6B—C1B0.57 (11)
C14A—C3A—C4A—C5A−177.67 (11)C17B—N2B—C6B—C1B179.20 (9)
C3A—C4A—C5A—C6A−0.34 (16)C4B—C5B—C6B—N2B−178.22 (11)
C7A—N2A—C6A—C5A179.04 (11)C4B—C5B—C6B—C1B2.09 (16)
C17A—N2A—C6A—C5A−0.97 (18)N1B—C1B—C6B—N2B−0.91 (12)
C7A—N2A—C6A—C1A−0.24 (11)C2B—C1B—C6B—N2B176.76 (10)
C17A—N2A—C6A—C1A179.75 (9)N1B—C1B—C6B—C5B178.85 (10)
C4A—C5A—C6A—N2A179.80 (11)C2B—C1B—C6B—C5B−3.48 (16)
C4A—C5A—C6A—C1A−1.02 (16)C1B—N1B—C7B—N2B−0.52 (12)
N1A—C1A—C6A—N2A0.51 (12)C1B—N1B—C7B—C8B179.13 (10)
C2A—C1A—C6A—N2A−178.94 (10)C6B—N2B—C7B—N1B−0.04 (12)
N1A—C1A—C6A—C5A−178.85 (10)C17B—N2B—C7B—N1B−178.57 (10)
C2A—C1A—C6A—C5A1.70 (17)C6B—N2B—C7B—C8B−179.69 (10)
C1A—N1A—C7A—N2A0.43 (12)C17B—N2B—C7B—C8B1.78 (17)
C1A—N1A—C7A—C8A179.73 (10)N1B—C7B—C8B—C9B−128.34 (12)
C6A—N2A—C7A—N1A−0.12 (12)N2B—C7B—C8B—C9B51.28 (16)
C17A—N2A—C7A—N1A179.90 (10)N1B—C7B—C8B—C13B48.53 (16)
C6A—N2A—C7A—C8A−179.40 (10)N2B—C7B—C8B—C13B−131.85 (12)
C17A—N2A—C7A—C8A0.61 (18)C13B—C8B—C9B—C10B1.75 (17)
N1A—C7A—C8A—C9A142.34 (12)C7B—C8B—C9B—C10B178.66 (10)
N2A—C7A—C8A—C9A−38.44 (17)C8B—C9B—C10B—C11B0.26 (17)
N1A—C7A—C8A—C13A−34.16 (16)C24B—O4B—C11B—C10B−0.90 (16)
N2A—C7A—C8A—C13A145.06 (11)C24B—O4B—C11B—C12B179.28 (11)
C13A—C8A—C9A—C10A−0.77 (17)C9B—C10B—C11B—O4B178.28 (10)
C7A—C8A—C9A—C10A−177.28 (10)C9B—C10B—C11B—C12B−1.91 (17)
C8A—C9A—C10A—C11A−0.42 (17)O4B—C11B—C12B—C13B−178.67 (11)
C24A—O4A—C11A—C10A0.81 (17)C10B—C11B—C12B—C13B1.50 (18)
C24A—O4A—C11A—C12A179.96 (11)C11B—C12B—C13B—C8B0.57 (19)
C9A—C10A—C11A—O4A−179.57 (11)C9B—C8B—C13B—C12B−2.17 (17)
C9A—C10A—C11A—C12A1.32 (17)C7B—C8B—C13B—C12B−179.17 (11)
O4A—C11A—C12A—C13A179.80 (11)C15B—O1B—C14B—O2B1.87 (17)
C10A—C11A—C12A—C13A−1.00 (18)C15B—O1B—C14B—C3B−176.53 (10)
C11A—C12A—C13A—C8A−0.22 (19)C2B—C3B—C14B—O2B13.21 (17)
C9A—C8A—C13A—C12A1.09 (17)C4B—C3B—C14B—O2B−162.95 (12)
C7A—C8A—C13A—C12A177.83 (11)C2B—C3B—C14B—O1B−168.41 (10)
C15A—O1A—C14A—O2A−1.09 (18)C4B—C3B—C14B—O1B15.43 (15)
C15A—O1A—C14A—C3A178.91 (10)C14B—O1B—C15B—C16B−81.55 (14)
C2A—C3A—C14A—O2A−1.66 (18)C6B—N2B—C17B—C18B75.69 (13)
C4A—C3A—C14A—O2A177.08 (12)C7B—N2B—C17B—C18B−106.01 (12)
C2A—C3A—C14A—O1A178.34 (10)N2B—C17B—C18B—C19B−178.22 (9)
C4A—C3A—C14A—O1A−2.92 (16)C23B—N3B—C19B—C18B122.57 (12)
C14A—O1A—C15A—C16A85.97 (14)C20B—N3B—C19B—C18B−59.60 (14)
C6A—N2A—C17A—C18A−77.35 (12)C17B—C18B—C19B—N3B−62.93 (12)
C7A—N2A—C17A—C18A102.63 (12)C23B—N3B—C20B—C21X−14.2 (3)
N2A—C17A—C18A—C19A179.58 (9)C19B—N3B—C20B—C21X167.8 (3)
C23A—N3A—C19A—C18A−119.70 (12)C23B—N3B—C20B—C21B18.41 (14)
C20A—N3A—C19A—C18A76.91 (13)C19B—N3B—C20B—C21B−159.62 (12)
C17A—C18A—C19A—N3A64.97 (12)N3B—C20B—C21B—C22B−26.58 (16)
C23A—N3A—C20A—C21A22.69 (14)C21X—C20B—C21B—C22B79.5 (4)
C19A—N3A—C20A—C21A−172.26 (10)N3B—C20B—C21X—C22B22.6 (3)
N3A—C20A—C21A—C22A−30.40 (13)C21B—C20B—C21X—C22B−60.1 (3)
C20A—C21A—C22A—C23A27.87 (13)C20B—C21B—C22B—C23B25.41 (16)
C19A—N3A—C23A—O3A8.94 (18)C20B—C21B—C22B—C21X−65.3 (3)
C20A—N3A—C23A—O3A173.68 (11)C20B—C21X—C22B—C21B73.6 (4)
C19A—N3A—C23A—C22A−169.69 (10)C20B—C21X—C22B—C23B−23.5 (3)
C20A—N3A—C23A—C22A−4.94 (13)C19B—N3B—C23B—O3B−4.92 (18)
C21A—C22A—C23A—O3A166.27 (12)C20B—N3B—C23B—O3B177.06 (11)
C21A—C22A—C23A—N3A−15.13 (13)C19B—N3B—C23B—C22B175.12 (10)
C7B—N1B—C1B—C2B−176.49 (11)C20B—N3B—C23B—C22B−2.90 (13)
C7B—N1B—C1B—C6B0.88 (12)C21B—C22B—C23B—O3B164.98 (14)
N1B—C1B—C2B—C3B178.73 (11)C21X—C22B—C23B—O3B−163.5 (2)
C6B—C1B—C2B—C3B1.58 (16)C21B—C22B—C23B—N3B−15.06 (15)
C1B—C2B—C3B—C4B1.46 (16)C21X—C22B—C23B—N3B16.5 (2)

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg4, Cg5 and Cg6 are the centroids of the N1B–N2B/C1B/C6B–C7B, C1A–C6A, C1B–C6B, C8B–C13B and C8A–C13A rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5A—H5AA···O3Bi0.952.303.2382 (15)171
C5B—H5BA···O3Aii0.952.383.3244 (15)172
C19A—H19A···O2Ai0.992.583.3034 (14)130
C19A—H19B···O3Bi0.992.533.2681 (15)131
C19B—H19C···O3Aii0.992.463.2007 (15)131
C9B—H9BA···Cg1iii0.952.853.5237 (12)129
C10B—H10B···Cg4iii0.952.803.4556 (12)127
C16A—H16B···Cg50.982.833.8093 (15)175
C18A—H18A···Cg6iv0.992.703.5251 (12)141
C24A—H24C···Cg2iv0.982.763.7186 (14)165

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) −x, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6575).

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